Process of preparing monobenzoyldiamino-anthraquinones



Patented July 12, 19332 HANS BUSES-332i, 013" LEVER-K'USEN-ON-THE-RI-II1 TE, HALTER MIEG, OF OPIiADE-N, AND

3s or LEVERKUSEN-OE-THE-RHINE, GERMANY, Assreuons TO Inn VJURKS, me, or new YGRK, n. Y., A oonronn'rron'or numb rnoonss or rnuranrns raononnuzornnreatruo enrrrnnouruonus No Drawing. Original application. filed November 21, less, serial No. 321,034 and i n Germany August so,

wherein one stands for hydrogen and the y 7 other to stands for the group lll-lUOsg ri In accordance with the invention l-ben zoylaminol-aminoanthraquinone and l-ben- Zoylamino-5-aminoanthraquinone are obtainable in a convenient manner and in a good yield by heating the corresponding diaminoanthraquinones in the presence of acid binding agent and of a suitable high boiling organic solvent being inert to the starting materials, such as nitrobenzene, ortho-dichlorobenzene, tric-hlorobenzene and the like, With benzoylchloride in av quantity corresponding to about ll40% of the theoretical amount. As acid binding agents suitable for performing our process alkali metal carbonates, magnesium oxide, calcium oxide, pyridine and its homologues, quinoline and the like may be mentioned by Way of example, from which in the case of .5-diamino-anthraquinone alkali metal carbonates, especially sodium carbonate in the case of 1.4L ciaminoanthraquinone sodium carbonate, pyridine or a homologue thereof will yield the best results.

The temperatures to be used may vary in 'WlClQ limits, mainly depending on the kind of diaminoanthraquinone and acid bindiilfid and this application filed March 13, 1930, Serial Ito. 435,630; g

by dissolving or distributing the dia'minoanthraquinone in the organic solvent, adding the acid bindingmedium in anamount at least sufficient to bind all of. the hydrochloric acid being liberated during the reaction, and then causing the benzoyl chloride to run in slowly While stirring and While heating the mixture to the temperatures above mentioned.

The Working up. of the reaction products Lifters according to the diaminoanthraluinones used as starting materials. When starting, for instance, with IA-diaminoan thraquinonathe reaction proceeds so smoothly. that ithout further treatment a technically valuable product results. In the case of 1.5ediaminoanthraquinone a fractional separation of the reaction product is necessary. In this case addition of analiphatic alcohol, especially ethyl alcohol, has'been found essential for carrying out the separation. process. By this'addition the small amounts of 1:5 dib-enZoyldiamino-anthra quinone, having been formed simultaneously with the nonobenzoyl compound. can be caused to separate, and from the filtrate the 1 benzoamino 5 aminoanthraquinone' can easily be isolated in a state of purity, sufficient for using the compound as intermediate product in the manufacture of dyestuffs Without any further cleaning. I r lhe following exampleillustrates vention Without limiting it thereto, the parts being by weight.- I

'Emmnpla 'loamixture of lOOxparts of 1.4l-diaminoanthraquinone and 500 parts of and p the mixture is heated to about 145450" 6., until all Water hasescaped. After quickly cooling to 15-20"G. 8O parts'of benzoylchloride, dissolved in 100 parts of nitro-f ben ene are gradually added, care being ta'lrenthat the temperature does not surmount 25 C. I After the addition of'the benzoyl chloride the. temperature is maintained at about 30 (1, until no more unchanged startmaterial is to be detected microscopically. The reaction product separates during the reaction and can be isolated by filtering.

our in- .2 in 1,867,058 I When working in this manner, the 1-benzoyl amino-4c-aminoanthraquinone of the formula:

m is obtained in a good yield and in a good state of purity. It is soluble in pyridine and sulfuric acid of 96% strength with a reddish-violet coloration and crystallizes from nitrobenzene in blue-black crystals.

'1 This is a division of our co-pending application Serial No. 321,034, filed November 21, 1928. v

We claim 1. Process for preparing l-benzoylaminog9. 4-aminoanthraquinone, which consists in slowly adding, while'stir'ring, benzoylchloride in aquantitycorresponding to 120140% of the theoretical amount, to a mixture of 1,4- diaminoanthraquinone, a high boiling organic solvent being inertto the starting materials and of anacid binding medium, while maintaining the temperature between about 1050 C.

2. Process for preparing l-benzoylamino- 7 3o i-aminoanthraquinone, which consists in slowly adding, While-stirring, benzoylchloride in a quantity corresponding to 120140% of the theoretical amount, to a mixture oil/1- diaminoanthraquinone, an organic solvent of the group consisting of nitrobenzene and ortho-dichlorobenzene, and of an acid binding medium of the group consisting of sodium carbonate, pyridine and its homologues, in an amount at least sufficient to bind all of the hydrochloric acid being liberated during the reaction, at a temperature of between about 1050 C.

3. Process which consists in heating a mixture of 100 parts by weight of lA-diamino- "anthra'quinone, 500 parts by weight of nitrobenzene and 135 parts by weight of collidine to about 145150 C. until all water has escaped, quickly cooling the mixture to 1520 C., slowly addingg'while stirring, a mixture of parts by weight of benzoylchloride and parts by Weight of nitrobenzene, care being taken that the temperature does not surmount 25 C., and heating the mixture after the addition of the benzoylchloride to about. 30 6., until no more unchanged starting material is to be detected microscopically. V In testimony whereof, we afiix our signatures. V 7 HANS BUCHLOH.

WALTER MIEG.

WALTHER STOETZER. 

